151490-40-3

Basic information

• Product Name: 2-(1-METHYL-1H-INDOL-3-YL)-2-OXOACETIC ACID METHYL ESTER
• Synonyms: METHYL 2-(1-METHYL-1H-INDOLE-3-YL)-2-OXOACETATE;METHYL (1-METHYLINDOLYL)-3-GLYOXYLATE;2-(1-METHYL-1H-INDOL-3-YL)-2-OXOACETIC ACID METHYL ESTER;METHYL (1-METHYLINDOLYL-3)-GLYOXYLATE, 9;Methyl (1-methylindolyl)-3-glyoxylate 97%;methyl 2-(1-methyl-1H-indol-3-yl)-2-oxoacetate
• CAS NO: 151490-40-3
• Molecular Formula: C₁₂H₁₁NO₃
• Molecular Weight: 217.22
• Product Categories: Aromatic Esters;Building Blocks;Heterocyclic Building Blocks;Indoles
• Mol File: 151490-40-3.mol
• Article Data: 18

Chemical Properties

• Melting Point: 96-100 °C(lit.)
• Boiling Point: 369.9°C at 760 mmHg
• Flash Point: 177.5°C
• Appearance: /
• Density: 1.21g/cm³
• Vapor Pressure: 1.15E-05mmHg at 25°C
• Refractive Index: 1.578
• CAS DataBase Reference: 2-(1-METHYL-1H-INDOL-3-YL)-2-OXOACETIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(1-METHYL-1H-INDOL-3-YL)-2-OXOACETIC ACID METHYL ESTER(151490-40-3)
• EPA Substance Registry System: 2-(1-METHYL-1H-INDOL-3-YL)-2-OXOACETIC ACID METHYL ESTER(151490-40-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 151490-40-3(Hazardous Substances Data)

Usage

Description

2-(1-METHYL-1H-INDOL-3-YL)-2-OXOACETIC ACID METHYL ESTER, also known as Methyl (1-methylindolyl)-3-glyoxylate, is an organic compound derived from 1-methylindole. It is characterized by its unique chemical structure, which features a methyl ester group and an indole ring, making it a versatile molecule for various applications in the pharmaceutical and chemical industries.

Uses

Used in Pharmaceutical Industry:
2-(1-METHYL-1H-INDOL-3-YL)-2-OXOACETIC ACID METHYL ESTER is used as a reactant for the synthesis of sotrastaurin analogs for its role in the development of novel protein kinase C (PKC) inhibitors. These inhibitors are crucial in the treatment of various diseases, including cancer and autoimmune disorders, due to their ability to modulate cellular signaling pathways.
Used in Chemical Synthesis:
In the chemical synthesis industry, 2-(1-METHYL-1H-INDOL-3-YL)-2-OXOACETIC ACID METHYL ESTER serves as a reactant for the preparation of indolyl diols. These compounds have potential applications in the development of new drugs and materials, thanks to their unique chemical properties and reactivity.
Overall, 2-(1-METHYL-1H-INDOL-3-YL)-2-OXOACETIC ACID METHYL ESTER is a valuable compound in both the pharmaceutical and chemical synthesis industries, owing to its diverse applications and the potential for further research and development in these fields.

InChI:InChI=1/C12H11NO3/c1-13-7-9(11(14)12(15)16-2)8-5-3-4-6-10(8)13/h3-7H,1-2H3

Upstream product

• 18372-22-0 2-(3-indolyl)oxoacetic acid methyl ester 
• 74-88-4 methyl iodide 
• 603-76-9 1-methylindole 
• 41600-21-9 methyl 2-oxo-2-(pyrrolidin-1-yl)acetate 
• 124-41-4 sodium methylate 
• 16382-38-0 1-methylindole-3-glyoxylyl chloride 
• 79-37-8 oxalyl dichloride 
• 120-72-9 indole 
• 22980-09-2 indolyl-3-glyoxylyl chloride 

Downstream Products

• 125313-98-6 3-(4-methoxyphenyl)-4-(1-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione 
• 125313-97-5 3-(1-methyl-3-indolyl)-4-phenyl-1H-pyrrole-2,5-dione 
• 170364-57-5 enzastaurin 
• 280744-09-4 SB-216763 
• 1262304-38-0 4-(4-(4-(3-(3-(4-(1-methyl-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl)-indol-1-yl)-propyl)-(1,2,3)triazol-1-yl)-phenyl)-butyric acid 
• 1262304-39-1 4-(4-(3-(3-(4-(1-methyl-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl)-indol-1-yl)-propyl)-(1,2,3)triazol-1-yl)-benzonitrile 
• 1262304-40-4 3-(1-methyl-1H-indol-3-yl)-4-(1-(3-(1-(4-nitro-phenyl)-1H-(1,2,3)triazol-4-yl)-propyl)-1H-indol-3-yl)-pyrrole-2,5-dione 
• 1262304-41-5 3-(1-(3-(1-(4-acetyl-phenyl)-1H-(1,2,3)triazol-4-yl)-propyl)-1H-indol-3-yl)-4-(1-methyl-1H-indol-3-yl)-pyrrole-2,5-dione 
• 1262304-43-7 (3-(4-(4-(3-(4-(1-methyl-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl)-indol-1-yl)-butyl)-(1,2,3)triazol-1-yl)-phenyl)-acetic acid 
• 1262304-42-6 (4-(4-(4-(3-(4-(1-methyl-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl)-indol-1-yl)-butyl)-(1,2,3)triazol-1-yl)-phenyl)-acetic acid 
• 1262304-44-8 4-(4-(4-(4-(3-(4-(1-methyl-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl)-indol-1-yl)-butyl)-(1,2,3)triazol-1-yl)-phenyl)-butyric acid 
• 125313-99-7 3-(4-chlorophenyl)-4-(1-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione 
• 125314-02-5 3-(4-aminophenyl)-4-(1-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione 

Relevant articles and documents

Synthesis and Evaluation of 3-(furo[2,3-b]pyridin-3-yl)-4-(1H-indol-3-yl)-maleimides as Novel GSK-3β Inhibitors and Anti-Ischemic Agents

A series of novel 3-(furo[2,3-b]pyridin-3-yl)-4-(1H-indol-3-yl)-maleimides were designed, synthesized, and biologically evaluated for their GSK-3β inhibitory activities. Most compounds showed favorable inhibitory activities against GSK-3β protein. Among them, compounds 5n, 5o, and 5p significantly reduced GSK-3β substrate tau phosphorylation at Ser396 in primary neurons, indicating inhibition of cellular GSK-3β activity. In the in vitro neuronal injury models, compounds 5n, 5o, and 5p prevented neuronal death against glutamate, oxygen-glucose deprivation, and nutrient serum deprivation which are closely associated with cerebral ischemic stroke. In the in vivo cerebral ischemia animal model, compound 5o reduced infarct size by 10% and improved the neurological deficit. The results may provide new insights into the development of novel GSK-3β inhibitors with potential neuroprotective activity against brain ischemic stroke.

Method for continuously preparing 3,4-(1-methyl-indol-3-yl)-1H-pyrrole-2,5-one compound by microchannel reactor

The invention discloses a method for continuously preparing a 3,4-(1-methyl-indol-3-yl)-1H-pyrrole-2,5-one compound by a microchannel reactor. The method comprises the following steps: dissolving 1-methyl-3-indole acetamide and 1-methyl indolo ketonic acid methyl ester into anhydrous dimethylformamide (DMF) to form a mixed solution which is a solution A; dissolving potassium tert-butoxide in anhydrous DMF, and uniformly carrying out mixing to obtain a solution B; and feeding the prepared solution A and the prepared solution B into the microchannel reactor for a reaction, enabling a reacted material liquid to flow out from an outlet of the microchannel reactor after the reaction process is finished, and carrying out post-treatment on the reacted material liquid to obtain the 3,4-(1-methyl-indol-3-yl)-1H-pyrrole-2,5-one compound. According to the method disclosed by the invention, the 3,4-(1-methyl-indol-3-yl)-1H-pyrrole-2,5-one is continuously prepared through the microchannel reactor,and the method has the advantages of mild conditions, high reaction speed, high yield, suitability for industrial production, and the like.

TARGETED PEPTIDE CONJUGATES

The present invention relates to the preparation and use of therapeutic compounds for the treatment of diseases at specific subcellular target areas such as specific cellular organelles. In particular, the therapeutic compounds of the invention are specific for modifying enzyme activity within targeted organelles or structures of cells and tissues. Subcellular organelles and structures that may be specifically targeted by compounds of the present invention include lysosomes, autophagasomes, the endoplasmic reticulum, the Golgi complex, peroxisomes, the nucleus, membranes and the mitochondria.

[18F]MALEIMIDE-BASED GLYCOGEN SYNTHASE KINASE-3BETA LIGANDS FOR POSITRON EMISSION TOMOGRAPHY IMAGING AND RADIOSYNTHESIS METHOD

The present invention provides a compound having the structure: (Formula I), and a method of inhibiting Glycogen synthase kinase-3 β (GSK-3β) in a subject comprising administering to the subject said compound, so as to thereby inhibit the GSK-3β in the subject.